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Chapter 29: Q25P (page 1179)

Outline the steps needed to synthesize the tetrapeptideAla–Leu–Ile–Gly using the Merrifield technique.

Short Answer

Expert verified

The synthesis of long peptides can be done by using Merrifield technique. It is a solid-phase technique.

An amino acid is attached to an insoluble polymer in the Merrifield method. Amino acids are sequentially added, one at a time, thereby forming successive peptide bonds.

Because impurities and by-products are not attached to the polymer chain, they are removed simply by washing them away with a solvent at each stage of the synthesis.

Step by step solution

01

Merrifield technique

The synthesis of long peptides can be done by using Merrifield technique. It is a solid-phase technique.

An amino acid is attached to an insoluble polymer in the Merrifield method. Amino acids are sequentially added, one at a time, thereby forming successive peptide bonds.

Because impurities and by-products are not attached to the polymer chain, they are removed simply by washing them away with a solvent at each stage of the synthesis.

02

Al-Leu-Ile-Gly

The given peptide has four amino acids in it. Hence it is an example of a tetrapeptide. The amino acids are alanine, leucine, isoleucine, and glycine.

03

Synthesis of the given tripeptide

The detailed synthesis of the given tetrapeptide in the solid phase is as shown below:

Synthesis of the given tetrapeptide

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Most popular questions from this chapter

Question:Draw the product formed when the following amino acid is treated with each reagent: (a) CH3OH;H+ (b) CH3COCl, pyridine; (c) HCl (1 equiv); (d) NaOH (1 equiv); (e).C6H5N=C=S

Question: Identify the nucleophile and the electrophile in the following acid–base reactions:

With reference to the following peptide:

(a) Identify the N-terminal and C-terminal amino acids.

(b) Name the peptide using one-letter abbreviations.

(c) Label all the amide bonds in the peptide backbone.

(a) What products are formed when each peptide is treated with trypsin? (b) What products are formed when each peptide is treated with chymotrypsin?

[1] Gly–Ala–Phe–Leu–Lys–Ala

[2] Phe–Tyr–Gly–Cys–Arg–Ser

[3] Thr–Pro–Lys–Glu–His–Gly–Phe–Cys–Trp–Val–Val–Phe

What is the predominant form of each of the following amino acids at pH=11? What is the overall charge on the amino acid? (a)valine; (b)proline; (c)glutamic acid; (d)lysine?
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